HCID 178454288, compound → HCID 178454287, compound

HRID 1497492Notes

Reaction equation

HRID 1497492 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9](=[N:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[NH:10][C:11]1[CH:38]=[CH:37][C:14]([C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][C:27]([O:29]CC3C=CC=CC=3)=[O:28])=[CH:20][CH:19]=2)=[O:16])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.[C].[Pd]>[C:43]([O:42][C:40]([NH:39][C:9](=[N:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[NH:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:20][CH:19]=2)=[O:16])=[CH:37][CH:38]=1)=[O:41])([CH3:46])([CH3:45])[CH3:44]

Participants

4

Reactant 1

HCID 178454288HCID 178454288, compound

Product 1

HCID 178454287HCID 178454287, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[4-(benzyloxy)-4-oxobutyl]phenyl 4-[N′,N″-bis(tert-butoxycarbonyl)carbamimidamido]benzoate (3.98 g) in tetrahydrofuran (40.0 mL) was added 10% palladium-carbon (398 mg), followed by stirring at room temperature for 3 hours under a hydrogen pressure of 3 atm. The reaction suspension was filtered through Celite, and then the filtrate was concentrated under reduced pressure to obtain 4-[4-({4-[N′,N″-bis(tert-butoxycarbonyl)carbamimidamido]benzoyl}oxy)phenyl]butanoic acid (3.30 g).

Workup

  1. filtrationThe reaction suspension was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8ba0f0b1b46f4bd8acd604ed3f4ccdc3
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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